Leesburg Airshow; hosted by Leesburg’s Parks and Recreation Department Sat, 26 Sep at 11:00 am Leesburg Municipal Airport-Godfrey Field AIR-SHOWS
38th Annual Leesburg Car Show Sat, 03 Oct at 12:00 pm 25 W Market St, Leesburg, VA 20176-2901, United States
Links On the Lawn: THE GREEN CARPET AFFAIR Sat, 26 Sep at 01:00 pm Stone Tower Winery USD 0 TO 10,673 MUSIC
PolicyMaker Series: Virginia's 10th Congressional District Candidates Debate Tue, 22 Sep at 08:00 am The National Conference Center SPORTS
Douglass Legacy Day Sat, 03 Oct at 12:00 pm 407 East Market Street, Leesburg, VA, United States, Virginia 20176 ART
The Reagan Years return to Tally Ho Theater on Saturday, Oct 10, 2026 Sat, 10 Oct at 08:00 pm Tally Ho Theater ART
Mamma Mania - The American Tribute to ABBA Fri, 23 Oct at 07:00 pm Tally Ho Theater USD 38 TO 79 MUSIC
Movie Night on the Lawn Fri, 02 Oct Fleetwood Farm Winery, Evergreen Mills Rd, Leesburg, VA, USA FREE FITNESS
Fall Paint & Sip at Fleetwood Fri, 09 Oct at 06:00 pm Fleetwood Farm Winery, Evergreen Mills Rd, Leesburg, VA, USA FREE FITNESS
High School Football: St John's Catholic vs. Loudoun Sports Academy (LSA) Fri, 25 Sep at 07:30 pm Segra Field SPORTS
Morven Park International Thu, 08 Oct at 08:00 am 41580 Sunday Morning Lane, Leesburg, VA, United States, Virginia 20176 SPORTS
Craftail Presents: Wicked Wreaths & Wine Sat, 26 Sep at 10:30 am Bleu Frog Vineyards & Ole Bleu Brewery USD 29 TO 55 FITNESS
Mushroomhead & Fear Factory at Tally Ho Theater Sun, 18 Oct at 06:00 pm Tally Ho Theater PERFORMANCES
Be Kind & Rewind: Ultimate 90s Experience Sat, 17 Oct at 07:00 pm Tally Ho Theater USD 22 TO 57 MUSIC
Wine Tasting & Pouring Paint on Pumpkins Fri, 25 Sep at 06:30 pm The King Street Experience USD 82 FITNESS
Spooky Sweets: A Halloween Mommy & Me Cake Pop Workshop Sun, 18 Oct at 10:00 am The Conche USD 50 WORKSHOPS
Leesburg Volunteer Fire Company Open House Sat, 03 Oct at 11:00 am 61 Plaza St NE , Leesburg, VA, United States, Virginia 20175 SHOPPING
Farmers Market at Fleetwood Sun, 11 Oct at 11:00 am Fleetwood Farm Winery, Evergreen Mills Rd, Leesburg, VA, USA FREE FITNESS
Author Event: Richard Chizmar Killing the Boogeyman Thu, 15 Oct at 06:30 pm 11 S King St, Leesburg, VA 20175, USA ART
Chocolate Boo Bash: A Mommy & Me Sculpting Workshop Sat, 24 Oct at 10:00 am The Conche USD 71 FITNESS
Sunset Pilates Class at Fleetwood Fri, 23 Oct at 06:00 pm Fleetwood Farm Winery, Evergreen Mills Rd, Leesburg, VA, USA FREE FITNESS
Boo’d Up: A Couples Halloween Experience Sat, 24 Oct at 05:00 pm Fleetwood Farm Winery USD 55 FITNESS
Friends of Homeless Animals Adoption Event Sun, 11 Oct Fleetwood Farm Winery, Evergreen Mills Rd, Leesburg, VA, USA FREE FITNESS
Sip & Bedazzle: A Rhinestone Workshop Sun, 27 Sep at 01:00 pm Black Hoof Brewing Company USD 50 WORKSHOPS
High School Football: St. James Performance Academy vs Loudoun Sports Academy (LSA) Fri, 30 Oct at 07:30 pm Segra Field SPORTS
Next Stop Comedy at Vanish Brewery in Lucketts! - Leesburg, VA Fri, 20 Jun at 08:00 pm Vanish Farmwoods Brewery USD 28 FITNESS
High School Football: MU Sports Academy vs Loudoun Sports Academy (LSA) Fri, 09 Oct at 07:30 pm Segra Field SPORTS
Gold Dust Woman: A Tribute to Stevie Nicks and Fleetwood Mac Sat, 07 Nov at 07:00 pm Tally Ho Theater USD 28 TO 63 MUSIC
A Grave Misunderstanding: M**der Mystery Dinner at The Branch Thu, 29 Oct at 06:00 pm The Branch USD 111 TO 123 FITNESS
Dance King Coffee + Cars Sat, 05 Sep 400 Madison Trade Plz SE, Leesburg, VA 20175-3761, United States SPORTS
16-Hours Interactive | CSM Certification Course in Leesburg, VA Thu, 25 Jun at 09:00 am Regus Center USD 675 TO 1,090 WORKSHOPS
2026 Leesburg Airshow - OFFICIAL EVENT Sat, 26 Sep at 11:00 am 1001 Sycolin Road, Leesburg, VA, United States, Virginia 20175 AIR-SHOWS
MIDNIGHT RELEASE: A Court of Splintered Harmony (ACOTAR 6) Mon, 26 Oct at 10:00 pm 9 W Market St, Leesburg, VA 20176, USA ART
High School Football: Friendship Collegiate vs Loudoun Sports Academy (LSA) Fri, 02 Oct at 08:00 pm Segra Field SPORTS
Free Chamber Music Concert: Mozart, Beethoven & Brahms Sat, 03 Oct at 07:00 pm Holy Trinity Lutheran Church FREE MUSIC
Princesses and Ponies Intro to Riding and Horsemanship Ages 3 and up Sun, 04 Oct at 10:00 am Hogback Mountain Pony Rides, LLC USD 135 FITNESS
Illustrator Event: Silent Nightmares, Illustrated by Orion Zangara Thu, 01 Oct at 06:30 pm 11 W Market St, Leesburg, VA 20176, USA ART
EnglishConnect en Leesburg Wed, 12 Aug La Iglesia de Jesucristo de los Santos de los Últimos Días — Edificio de Leesburg FREE FITNESS
🎃🕸️ Halloween Music Bingo at The Branch 🕸️🎃 Thu, 22 Oct at 07:00 pm 49 Catoctin Circle SE, Leesburg, VA BINGO
Beginner-Friendly American Mahjong Social League Sat, 17 Oct at 01:00 pm The King Street Experience CONTESTS
High School Football: Mt. Zion Prep vs Loudoun Sports Academy (LSA) Fri, 16 Oct at 07:30 pm Segra Field SPORTS
The Ultimate 2000's Dance Party with So Fetch Fri, 13 Nov at 07:00 pm Tally Ho Theater USD 31 TO 54 MUSIC
Paws and Paints @Vanish Farmwood Brewery Fri, 16 Oct at 06:30 pm Vanish Farmwoods Brewery USD 50 FITNESS
Loudoun Thrift October Mobile Thrift Tour Sat, 10 Oct at 09:00 am Meetup at First Stop Blue Ridge Care Thrift USD 109 FITNESS
🍂☕ Cozy Fall Music Bingo at The Branch ☕🍂 Thu, 08 Oct at 07:00 pm 49 Catoctin Circle SE, Leesburg, VA BINGO
LVFC Big House Classic Golf Tournament 2026 Fri, 25 Sep at 09:30 am Raspberry Falls Golf & Hunt Club SPORTS
High School Football: Riverdale Baptist vs Loudoun Sports Academy (LSA) Fri, 23 Oct at 08:00 pm Segra Field SPORTS
Bark to School: Meet Dog Man at Rust Library! Sun, 27 Sep at 03:00 pm 380 Old Waterford Rd NW, Leesburg, VA 20176, USA DOG